#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/86/2228607.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228607
loop_
_publ_author_name
'He, Long'
_publ_section_title
;
 Diethyl 4-acetyl-5-(2-nitrophenyl)pyrrolidine-2,2-dicarboxylate
;
_journal_coeditor_code           XU5078
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3205
_journal_paper_doi               10.1107/S1600536810045691
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H22 N2 O7'
_chemical_formula_moiety         'C18 H22 N2 O7'
_chemical_formula_sum            'C18 H22 N2 O7'
_chemical_formula_weight         378.38
_chemical_name_systematic
;
Diethyl 4-acetyl-5-(2-nitrophenyl)pyrrolidine-2,2-dicarboxylate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 97.455(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            2
_cell_length_a                   10.687(5)
_cell_length_b                   7.760(5)
_cell_length_c                   12.030(5)
_cell_measurement_reflns_used    11509
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.3291
_cell_measurement_theta_min      4.1683
_cell_volume                     989.2(9)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S Ultra'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0099
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19238
_diffrn_reflns_theta_full        72.58
_diffrn_reflns_theta_max         72.58
_diffrn_reflns_theta_min         4.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  0.7888
_exptl_absorpt_correction_T_min  0.7432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.420
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2105
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0807
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0250P)²+1.3702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.1660
_reflns_number_gt                1915
_reflns_number_total             2105
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5078.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2228607
_cod_database_fobs_code          2228607
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O3 0.0038(5) 0.2421(8) 0.5230(4) 0.0881(16) Uani d . 1 . .
N N2 0.2698(5) 0.3189(8) 0.6658(4) 0.0681(15) Uani d D 1 . .
O O5 0.1828(5) 0.4223(10) 0.8609(6) 0.117(2) Uani d U 1 . .
C C3 0.2453(6) 0.4941(9) 0.4653(6) 0.0641(16) Uani d . 1 . .
H H3 0.1941 0.5184 0.5202 0.077 Uiso calc R 1 . .
O O1 0.4209(6) 0.0223(8) 0.4138(5) 0.0957(18) Uani d . 1 . .
C C2 0.3126(5) 0.3415(9) 0.4718(5) 0.0566(14) Uani d . 1 . .
O O6 0.4399(5) 0.1838(10) 0.8411(4) 0.108(2) Uani d . 1 . .
O O4 0.0249(5) 0.2457(11) 0.8118(5) 0.112(2) Uani d . 1 . .
O O2 0.5571(5) 0.1618(10) 0.3371(5) 0.120(2) Uani d . 1 . .
C C8 0.1956(6) 0.0846(9) 0.5533(5) 0.0631(16) Uani d . 1 . .
H H8 0.2247 -0.0192 0.5180 0.076 Uiso calc R 1 . .
N N1 0.4602(6) 0.1556(10) 0.3797(5) 0.0784(17) Uani d . 1 . .
C C7 0.3030(5) 0.2205(9) 0.5697(4) 0.0589(15) Uani d . 1 . .
H H7 0.3841 0.1624 0.5905 0.071 Uiso calc R 1 . .
C C1 0.3875(5) 0.3157(10) 0.3870(5) 0.0605(15) Uani d . 1 . .
C C16 0.1311(7) 0.2862(12) 0.8096(6) 0.079(2) Uani d . 1 . .
C C4 0.2514(6) 0.6116(10) 0.3802(6) 0.0776(19) Uani d . 1 . .
H H4 0.2028 0.7113 0.3771 0.093 Uiso calc R 1 . .
C C12 0.0663(7) 0.1228(11) 0.3583(5) 0.085(2) Uani d . 1 . .
H H12A -0.0097 0.1760 0.3228 0.128 Uiso calc R 1 . .
H H12B 0.0620 0.0007 0.3455 0.128 Uiso calc R 1 . .
H H12C 0.1375 0.1694 0.3274 0.128 Uiso calc R 1 . .
C C11 0.0803(6) 0.1578(9) 0.4820(5) 0.0649(16) Uani d . 1 . .
O O7 0.2881(6) 0.0324(11) 0.9076(6) 0.130(2) Uani d U 1 . .
C C10 0.2269(6) 0.1943(11) 0.7453(5) 0.0721(19) Uani d . 1 . .
C C6 0.3975(6) 0.4353(11) 0.3036(6) 0.0732(19) Uani d . 1 . .
H H6 0.4511 0.4149 0.2500 0.088 Uiso calc R 1 . .
C C13 0.3357(7) 0.1387(14) 0.8371(6) 0.092(2) Uani d U 1 . .
C C9 0.1723(8) 0.0442(10) 0.6740(5) 0.080(2) Uani d . 1 . .
H H9A 0.0826 0.0330 0.6782 0.096 Uiso calc R 1 . .
H H9B 0.2137 -0.0625 0.6995 0.096 Uiso calc R 1 . .
C C5 0.3294(7) 0.5809(11) 0.3001(6) 0.084(2) Uani d . 1 . .
H H5 0.3350 0.6611 0.2435 0.101 Uiso calc R 1 . .
C C17 0.1066(10) 0.5318(17) 0.9259(8) 0.128(3) Uani d DU 1 . .
H H17A 0.0174 0.5231 0.8985 0.154 Uiso calc R 1 . .
H H17B 0.1325 0.6515 0.9246 0.154 Uiso calc R 1 . .
C C14 0.3850(10) -0.0385(18) 1.0007(8) 0.137(3) Uani d DU 1 . .
H H14A 0.3874 -0.1634 0.9994 0.165 Uiso calc R 1 . .
H H14B 0.4687 0.0064 0.9954 0.165 Uiso calc R 1 . .
C C15 0.3341(11) 0.0277(19) 1.1036(8) 0.153(3) Uani d DU 1 . .
H H15A 0.3856 -0.0141 1.1694 0.229 Uiso calc R 1 . .
H H15B 0.2490 -0.0121 1.1036 0.229 Uiso calc R 1 . .
H H15C 0.3352 0.1514 1.1034 0.229 Uiso calc R 1 . .
C C18 0.1366(11) 0.455(2) 1.0415(9) 0.158(3) Uani d DU 1 . .
H H18A 0.0896 0.5141 1.0925 0.237 Uiso calc R 1 . .
H H18B 0.2253 0.4664 1.0663 0.237 Uiso calc R 1 . .
H H18C 0.1141 0.3350 1.0391 0.237 Uiso calc R 1 . .
H H10 0.342(4) 0.377(8) 0.693(5) 0.07(2) Uiso d D 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N2 C10 . . 107.3(6) ?
C7 N2 H10 . . 105(4) ?
C10 N2 H10 . . 114(4) ?
C16 O5 C17 . . 119.2(7) ?
C4 C3 C2 . . 122.3(6) ?
C4 C3 H3 . . 118.9 ?
C2 C3 H3 . . 118.9 ?
C3 C2 C1 . . 115.3(6) ?
C3 C2 C7 . . 119.1(5) ?
C1 C2 C7 . . 125.6(6) ?
C11 C8 C9 . . 113.0(5) ?
C11 C8 C7 . . 110.5(5) ?
C9 C8 C7 . . 103.1(5) ?
C11 C8 H8 . . 110.0 ?
C9 C8 H8 . . 110.0 ?
C7 C8 H8 . . 110.0 ?
O1 N1 O2 . . 122.1(8) ?
O1 N1 C1 . . 119.4(6) ?
O2 N1 C1 . . 118.5(8) ?
N2 C7 C2 . . 109.7(6) ?
N2 C7 C8 . . 101.8(5) ?
C2 C7 C8 . . 116.4(4) ?
N2 C7 H7 . . 109.6 ?
C2 C7 H7 . . 109.6 ?
C8 C7 H7 . . 109.6 ?
C6 C1 C2 . . 122.8(7) ?
C6 C1 N1 . . 115.6(6) ?
C2 C1 N1 . . 121.6(6) ?
O4 C16 O5 . . 123.5(8) ?
O4 C16 C10 . . 126.3(8) ?
O5 C16 C10 . . 110.1(6) ?
C5 C4 C3 . . 119.8(7) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O3 C11 C12 . . 121.3(7) ?
O3 C11 C8 . . 121.1(6) ?
C12 C11 C8 . . 117.6(6) ?
C13 O7 C14 . . 114.4(7) ?
N2 C10 C9 . . 105.4(5) ?
N2 C10 C16 . . 107.8(6) ?
C9 C10 C16 . . 114.1(6) ?
N2 C10 C13 . . 112.0(6) ?
C9 C10 C13 . . 112.7(7) ?
C16 C10 C13 . . 104.9(5) ?
C5 C6 C1 . . 119.7(6) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
O6 C13 O7 . . 127.1(9) ?
O6 C13 C10 . . 124.7(9) ?
O7 C13 C10 . . 108.2(7) ?
C10 C9 C8 . . 106.3(6) ?
C10 C9 H9A . . 110.5 ?
C8 C9 H9A . . 110.5 ?
C10 C9 H9B . . 110.5 ?
C8 C9 H9B . . 110.5 ?
H9A C9 H9B . . 108.7 ?
C6 C5 C4 . . 120.0(7) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
O5 C17 C18 . . 101.2(9) ?
O5 C17 H17A . . 111.5 ?
C18 C17 H17A . . 111.5 ?
O5 C17 H17B . . 111.5 ?
C18 C17 H17B . . 111.5 ?
H17A C17 H17B . . 109.3 ?
C15 C14 O7 . . 101.4(8) ?
C15 C14 H14A . . 111.5 ?
O7 C14 H14A . . 111.5 ?
C15 C14 H14B . . 111.5 ?
O7 C14 H14B . . 111.5 ?
H14A C14 H14B . . 109.3 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 C11 . 1.202(8) ?
N2 C7 . 1.467(8) ?
N2 C10 . 1.474(9) ?
N2 H10 . 0.92(5) ?
O5 C16 . 1.308(10) ?
O5 C17 . 1.470(11) ?
C3 C4 . 1.378(9) ?
C3 C2 . 1.383(9) ?
C3 H3 . 0.9300 ?
O1 N1 . 1.208(9) ?
C2 C1 . 1.390(8) ?
C2 C7 . 1.521(8) ?
O6 C13 . 1.162(9) ?
O4 C16 . 1.181(8) ?
O2 N1 . 1.214(7) ?
C8 C11 . 1.517(8) ?
C8 C9 . 1.537(8) ?
C8 C7 . 1.552(8) ?
C8 H8 . 0.9800 ?
N1 C1 . 1.474(9) ?
C7 H7 . 0.9800 ?
C1 C6 . 1.382(9) ?
C16 C10 . 1.536(10) ?
C4 C5 . 1.375(9) ?
C4 H4 . 0.9300 ?
C12 C11 . 1.501(9) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
O7 C13 . 1.330(11) ?
O7 C14 . 1.525(11) ?
C10 C9 . 1.518(10) ?
C10 C13 . 1.557(10) ?
C6 C5 . 1.342(11) ?
C6 H6 . 0.9300 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C5 H5 . 0.9300 ?
C17 C18 . 1.509(9) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C14 C15 . 1.506(9) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H10 O2 2_656 0.92(5) 2.51(6) 3.244(9) 138(5)
C18 H18A O4 2_557 0.96 2.53 3.460(15) 162(6)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 C3 C2 C1 . . . . 0.5(9) ?
C4 C3 C2 C7 . . . . 178.7(6) ?
C10 N2 C7 C2 . . . . 164.3(5) ?
C10 N2 C7 C8 . . . . 40.5(6) ?
C3 C2 C7 N2 . . . . -25.6(7) ?
C1 C2 C7 N2 . . . . 152.3(6) ?
C3 C2 C7 C8 . . . . 89.2(7) ?
C1 C2 C7 C8 . . . . -92.9(7) ?
C11 C8 C7 N2 . . . . 84.9(6) ?
C9 C8 C7 N2 . . . . -36.2(6) ?
C11 C8 C7 C2 . . . . -34.3(8) ?
C9 C8 C7 C2 . . . . -155.3(6) ?
C3 C2 C1 C6 . . . . 1.7(9) ?
C7 C2 C1 C6 . . . . -176.3(6) ?
C3 C2 C1 N1 . . . . -177.2(6) ?
C7 C2 C1 N1 . . . . 4.8(9) ?
O1 N1 C1 C6 . . . . -148.9(7) ?
O2 N1 C1 C6 . . . . 29.6(9) ?
O1 N1 C1 C2 . . . . 30.0(10) ?
O2 N1 C1 C2 . . . . -151.4(6) ?
C17 O5 C16 O4 . . . . 0.4(13) ?
C17 O5 C16 C10 . . . . 178.7(7) ?
C2 C3 C4 C5 . . . . -2.0(11) ?
C9 C8 C11 O3 . . . . 30.1(9) ?
C7 C8 C11 O3 . . . . -84.8(8) ?
C9 C8 C11 C12 . . . . -150.7(6) ?
C7 C8 C11 C12 . . . . 94.4(7) ?
C7 N2 C10 C9 . . . . -28.4(7) ?
C7 N2 C10 C16 . . . . -150.7(5) ?
C7 N2 C10 C13 . . . . 94.5(7) ?
O4 C16 C10 N2 . . . . 120.5(8) ?
O5 C16 C10 N2 . . . . -57.8(8) ?
O4 C16 C10 C9 . . . . 3.7(11) ?
O5 C16 C10 C9 . . . . -174.5(7) ?
O4 C16 C10 C13 . . . . -120.0(9) ?
O5 C16 C10 C13 . . . . 61.8(9) ?
C2 C1 C6 C5 . . . . -2.4(10) ?
N1 C1 C6 C5 . . . . 176.5(7) ?
C14 O7 C13 O6 . . . . -1.7(14) ?
C14 O7 C13 C10 . . . . 178.0(8) ?
N2 C10 C13 O6 . . . . -2.8(12) ?
C9 C10 C13 O6 . . . . 115.9(10) ?
C16 C10 C13 O6 . . . . -119.5(10) ?
N2 C10 C13 O7 . . . . 177.5(7) ?
C9 C10 C13 O7 . . . . -63.8(8) ?
C16 C10 C13 O7 . . . . 60.8(9) ?
N2 C10 C9 C8 . . . . 4.1(8) ?
C16 C10 C9 C8 . . . . 122.2(6) ?
C13 C10 C9 C8 . . . . -118.4(6) ?
C11 C8 C9 C10 . . . . -99.6(7) ?
C7 C8 C9 C10 . . . . 19.7(7) ?
C1 C6 C5 C4 . . . . 0.8(11) ?
C3 C4 C5 C6 . . . . 1.3(11) ?
C16 O5 C17 C18 . . . . 93.1(11) ?
C13 O7 C14 C15 . . . . 119.5(10) ?
